Hydrochloric Acid → HCID 2749419, compound

HRID 1034118Notes

Reaction equation

HRID 1034118 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.B(Br)(Br)Br.[OH-].[K+].Cl>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 25134Boron tribromideHCID 6108741-Methoxy-2-(2-phenylethenyl)benzene

Product 1

HCID 2749419HCID 2749419, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In an atmosphere of nitrogen, 7.75 g (36.9 mmol) of 2-methoxystilbene (c-2) is dissolved in anhydrous dichloromethane. Fourty milliliters of a dichloromethane solution containing 3.2 g (12.9 mmol) of boron tribromide is added dropwise thereto at -78° C. (on a dry ice-acetone bath), followed by stirring overnight at room temperature. The reaction solution is cooled on an ice bath, and a 10% aqueous solution of KOH is added thereto drop by drop to decompose a boron complex formed in the reaction solution. This reaction solution is transferred to a separatory funnel, and 2M HCl is added thereto until the aqueous layer becomes acidic. The resulting solution is extracted with three 200 ml portions of chloroform. The chloroform layer is washed with two 50 ml portions of water and dried over anhydrous Na2SO4, followed by filtration. When the solvent is removed by distillation under reduced pressure, a brown oily product containing 2-hydroxystilbene (d-2) is obtained. This oily product is purified by column chromatography [SiO2 : 200 g, hexane-ethyl acetate (9:1 v/v)], and further recrystallized from hexane-ethyl acetate, thereby obtaining 5.05 g (yield: 69.9%) of 2-hydroxystilbene (d-2) (sample No. 9) as white needle crystals (melting point: 138°-139° C.).

Workup

  1. additionis added dropwise
  2. customat -78° C.
  3. temperatureThe reaction solution is cooled on an ice bath
  4. customformed in the reaction solution
  5. customThis reaction solution is transferred to a separatory funnel
  6. extractionThe resulting solution is extracted with three 200 ml portions of chloroform
  7. washThe chloroform layer is washed with two 50 ml portions of water
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfollowed by filtration
  10. customWhen the solvent is removed by distillation under reduced pressure
  11. additiona brown oily product containing 2-hydroxystilbene (d-2)
  12. customis obtained
  13. customThis oily product is purified by column chromatography [SiO2 : 200 g, hexane-ethyl acetate (9:1 v/v)]
  14. customfurther recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-aaf021a63de243d2850530ac3616fb58
Source dataset
uspto-grants-1994_05
Patent number
US05314693

Reaction notes

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